US4816060A - Herbicidal aqueous compositions of imidazolinone herbicides - Google Patents
Herbicidal aqueous compositions of imidazolinone herbicides Download PDFInfo
- Publication number
- US4816060A US4816060A US06/896,775 US89677586A US4816060A US 4816060 A US4816060 A US 4816060A US 89677586 A US89677586 A US 89677586A US 4816060 A US4816060 A US 4816060A
- Authority
- US
- United States
- Prior art keywords
- acid
- methyl
- oxo
- isopropyl
- imidazolin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical group O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 230000002363 herbicidal effect Effects 0.000 title claims description 9
- 239000004009 herbicide Substances 0.000 title abstract description 3
- 239000002253 acid Substances 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 10
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical class OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- KCTKQZUYHSKJLP-UHFFFAOYSA-N 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylate;propan-2-ylazanium Chemical compound CC(C)[NH3+].N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C([O-])=O KCTKQZUYHSKJLP-UHFFFAOYSA-N 0.000 claims 2
- QRSHQJLLXXEYPS-UHFFFAOYSA-N azane;5-ethyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound [NH4+].[O-]C(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 QRSHQJLLXXEYPS-UHFFFAOYSA-N 0.000 claims 2
- FBJUTZMAUXJMMH-UHFFFAOYSA-N azane;5-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound [NH4+].N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C([O-])=O FBJUTZMAUXJMMH-UHFFFAOYSA-N 0.000 claims 2
- VJBCNMFKFZIXHC-UHFFFAOYSA-N azanium;2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)quinoline-3-carboxylate Chemical compound N.N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O VJBCNMFKFZIXHC-UHFFFAOYSA-N 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 8
- -1 trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy Chemical group 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000002636 imidazolinyl group Chemical group 0.000 description 4
- 229960003512 nicotinic acid Drugs 0.000 description 4
- 235000001968 nicotinic acid Nutrition 0.000 description 4
- 239000011664 nicotinic acid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000006353 oxyethylene group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910052717 sulfur Chemical group 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
- QDXJFRHCHWDQSP-UHFFFAOYSA-N 1,4-dihydroimidazol-5-one;quinoline Chemical class O=C1CNC=N1.N1=CC=CC2=CC=CC=C21 QDXJFRHCHWDQSP-UHFFFAOYSA-N 0.000 description 1
- VSGNJFMJPJJRTQ-UHFFFAOYSA-N 2-(4,5-dihydroimidazol-1-yl)benzoic acid Chemical class OC(=O)C1=CC=CC=C1N1C=NCC1 VSGNJFMJPJJRTQ-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Definitions
- Novel imidazolinyl benzoic acids, esters and salts, their preparation and use are disclosed in U.S. Pat. Nos. 4,188,487; 4,297,128 and 4,554,013 and pending application for U.S. Letters Patent Ser. Nos. 579,224, and 629,296, while various novel pyridine and quinoline imidazolinone compounds are described in pending application for U.S. Letters Patent Ser. No. 382,041, and U.S. Pat. Nos. 4,647,301, 4,650,514, 4,608,079 and 4,701,208.
- W is oxygen or sulfur
- X is H, halogen, methyl or hydroxyl
- Y and Z are each hydrogen, halogen, C 1 -C 6 alkyl, hydroxyloweralkyl, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, phenoxy, C 1 -C 4 haloalkyl, nitro, cyano, C 1 -C 4 alkylamino, diloweralkylamino or C 1 -C 4 alkylsulfonyl group; or phenyl optionally substituted with C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; difluoromethoxy, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, C 3 -C 8 straight or branched alkenyloxy optionally substituted with one to three halogens, or C 3 -C 8 straight or branched alkynyloxy optionally substituted with one to three halogens; and, when taken together, Y and Z may form a ring which may
- R 1 is C 1 -C 4 alkyl
- R 2 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; and when R 1 and R 2 are taken together with the carbon to which they are attached they may represent C 3 -C 6 cycloalkyl optionally substituted with methyl.
- Acids of formula I may be formulated as aqueous solutions of a water soluble salt of the acid, as they have limited solubility in non-protic organic solvents.
- the preparation of organic solvent emulsifiable compositions of formula I acids by utilizing C 8 to C 22 tertiary alkylamine salts of the acid which are soluble in organic solvents is described in pending application for U.S. Letters Patent of B. Cross and W. Sachr, Ser. No. 734,212 filed May 15, 1985.
- the present invention is novel aqueous herbicidal compositions comprising on a weight basis 1.0% to 45% of a water soluble salt of a formula I imidazolinone acid; 0 to 20% of urea; 0% to 30% of a nonionic surfactant; and sufficient water to total 100% which have been buffered with a sufficient amount of acid to have an initial pH in a range of about from pH 6 to pH 8.5.
- aqueous compositions of water soluble acid salts of formula I imidazolinyl salts is improved by stabilizing the initial pH of the aqueous compositions with sufficient amounts of a mineral or water soluble organic acid to a pH about equal to the pH of the formula I acid which is normally in a range of about pH 6 to pH 8.5 and preferably pH 7 to pH 7.5.
- Preferred acids for use in the compositions of the invention include hydrochloric acid, phosphoric acid, sulfuric acid, acetic acid, propionic acid and the like with acetic acid being most preferred.
- urea as an antifreezing agent to aqueous compositions of the invention in amounts of from 15% to 20% on a weight basis also improves the freeze-thaw characteristics of the compositions of the present invention, in that any solids which form during freezing readily redissolve on standing.
- Prior reference to the use of urea to improve cold stabilization of aqueous pyrazolium salt compositions may be found in U.S. Pat. No. 4,529,436.
- Surfactants suitable for use in the compositions of this invention are in general non-ionic surfactants with polyoxyethylene glycols, polyoxyethylene sorbitan monolaurates and dialkylphenoxypolyethylineoxyethanols being preferred.
- Salts of formula I compounds which find utility in the compositions of this invention are in general those which have sufficient water solubility to provide about 1% to 50% aqueous solution of the acid as the salt, with sodium, potassium, ammonium and water soluble organic ammonium being preferred and sodium, potassium, ammonium and isopropylammonium being most preferred.
- imidazolinyl acids listed in Table I below are added at ambient temperature to a stirred water solution containing 1.0 to 1.10 equivalents of the desired base and the desired quantity of urea and surfactant.
- the resulting mixture is agitated until complete solution of the acid is obtained.
- the pH of the solution is adjusted to the desired pH range by the addition of mineral or organic acids to the stirred solution followed by the addition of water to obtain the desired final concentration of ingredients.
- compositions prepared in Example 1 above are stored at 25° C., 37° C. and 45° C. Samples are withdrawn and the weight percent decomposition of the active formula I herbicide determined.
- Table II The results of these experiments which are summarized in Table II below demonstrate the improvement in stability of aqueous compositions which have their initial pH adjusted and stabilized by the addition of acid.
- compositions prepared by the procedure of Example 1 containing varying percentages of urea are cooled until precipitation of solids occurs.
- the samples are allowed to stand and are monitored until the temperature at which a complete solution is obtained and recorded.
- the results of these experiments are summarized in Table III below.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/896,775 US4816060A (en) | 1986-08-15 | 1986-08-15 | Herbicidal aqueous compositions of imidazolinone herbicides |
| AT87111215T ATE72727T1 (de) | 1986-08-15 | 1987-08-04 | Herbizide, waesserige zusammensetzungen von imidazolinonherbiziden. |
| ES198787111215T ES2037686T3 (es) | 1986-08-15 | 1987-08-04 | Composiciones acuosas herbicidas de imidazolinona. |
| DE8787111215T DE3776833D1 (de) | 1986-08-15 | 1987-08-04 | Herbizide, waesserige zusammensetzungen von imidazolinonherbiziden. |
| EP87111215A EP0256414B1 (en) | 1986-08-15 | 1987-08-04 | Herbicidal aqueous compositions of imidazolinone herbicides |
| IL83461A IL83461A (en) | 1986-08-15 | 1987-08-06 | Herbicidal aqueous compositions of imidazolinone herbicides |
| IN624/CAL/87A IN166550B (ru) | 1986-08-15 | 1987-08-11 | |
| TR87/0569A TR24598A (tr) | 1986-08-15 | 1987-08-12 | Imidazolinon herbisidlerin herbisidal sulu terkipleri |
| CS875979A CS271478B2 (en) | 1986-08-15 | 1987-08-13 | Aqueous herbicide |
| CA000544404A CA1297695C (en) | 1986-08-15 | 1987-08-13 | Herbicidal aqueous compositions of imidazolinone herbicides |
| EG469/87A EG18433A (en) | 1986-08-15 | 1987-08-13 | Herbicidal aqueous compositions of imidazolinone herbicides |
| YU151187A YU46560B (sh) | 1986-08-15 | 1987-08-13 | Postupak za povećanje stabilnosti vodenih rastvora soli imidazolinonskih kiselina |
| SI8711511A SI8711511A8 (sl) | 1986-08-15 | 1987-08-13 | Postopek za povečanje stabilnosti vodnih raztopin soli imidazolinonskih kislin |
| SU874203183A SU1723994A3 (ru) | 1986-08-15 | 1987-08-14 | Гербицидна композици |
| BG080934A BG48203A3 (en) | 1986-08-15 | 1987-08-14 | Herbicide aqueous composition |
| UA4203183A UA6153A1 (ru) | 1986-08-15 | 1987-08-14 | Гербицидная композиция |
| HU873684A HU200888B (en) | 1986-08-15 | 1987-08-14 | Process for producing aquous composition of imidazolinone herbicides |
| IE217687A IE61158B1 (en) | 1986-08-15 | 1987-08-14 | Herbicidal aqueous compositions of imidazolinone herbicides |
| AU76892/87A AU597407B2 (en) | 1986-08-15 | 1987-08-14 | Herbicidal aqueous compositions of imidazolinone herbicides |
| KR1019870008947A KR950006916B1 (ko) | 1986-08-15 | 1987-08-14 | 이미다졸리논 제초제의 제초성 수성 조성물 |
| JP62201952A JP2512759B2 (ja) | 1986-08-15 | 1987-08-14 | イミダゾリノン除草剤類の水性除草剤組成物類 |
| DK198704257A DK174864B1 (da) | 1986-08-15 | 1987-08-14 | Vandige herbicidpræparater indeholdende imidazolinonherbicider |
| ZA876050A ZA876050B (en) | 1986-08-15 | 1987-08-14 | Herbicidal aqueous compositions of imidazolinone herbicides |
| DD87306062A DD261518A5 (de) | 1986-08-15 | 1987-08-14 | Waessrige herbizide zusammensetzungen |
| BR8704215A BR8704215A (pt) | 1986-08-15 | 1987-08-14 | Composicao herbicida |
| GR910401738T GR3003891T3 (ru) | 1986-08-15 | 1992-02-27 | |
| LTRP987A LT2508B (lt) | 1986-08-15 | 1993-09-16 | Herbicidine kompozicija |
| LV931139A LV5649A3 (lv) | 1986-08-15 | 1993-10-08 | Herbicida kompozicija |
| GEAP19941747A GEP19970806B (en) | 1986-08-15 | 1994-01-20 | Herbicidal imidazolinone composition |
| MD94-0093A MD99C2 (ru) | 1986-08-15 | 1994-04-27 | Гербицидная композиция |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/896,775 US4816060A (en) | 1986-08-15 | 1986-08-15 | Herbicidal aqueous compositions of imidazolinone herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4816060A true US4816060A (en) | 1989-03-28 |
Family
ID=25406812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/896,775 Expired - Lifetime US4816060A (en) | 1986-08-15 | 1986-08-15 | Herbicidal aqueous compositions of imidazolinone herbicides |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4816060A (ru) |
| EP (1) | EP0256414B1 (ru) |
| JP (1) | JP2512759B2 (ru) |
| KR (1) | KR950006916B1 (ru) |
| AT (1) | ATE72727T1 (ru) |
| AU (1) | AU597407B2 (ru) |
| BG (1) | BG48203A3 (ru) |
| BR (1) | BR8704215A (ru) |
| CA (1) | CA1297695C (ru) |
| CS (1) | CS271478B2 (ru) |
| DD (1) | DD261518A5 (ru) |
| DE (1) | DE3776833D1 (ru) |
| DK (1) | DK174864B1 (ru) |
| EG (1) | EG18433A (ru) |
| ES (1) | ES2037686T3 (ru) |
| GE (1) | GEP19970806B (ru) |
| GR (1) | GR3003891T3 (ru) |
| HU (1) | HU200888B (ru) |
| IE (1) | IE61158B1 (ru) |
| IL (1) | IL83461A (ru) |
| IN (1) | IN166550B (ru) |
| SU (1) | SU1723994A3 (ru) |
| TR (1) | TR24598A (ru) |
| UA (1) | UA6153A1 (ru) |
| YU (1) | YU46560B (ru) |
| ZA (1) | ZA876050B (ru) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4936902A (en) * | 1989-04-25 | 1990-06-26 | American Cyanamid Company | Selective control of sicklepod in the presence of leguminous crops |
| US5268352A (en) * | 1989-11-22 | 1993-12-07 | American Cyanamid Company | Herbicidal emulsifiable suspension concentrate compositions |
| US5283335A (en) * | 1990-08-31 | 1994-02-01 | American Cyanamid Company | Herbicidal 2-(2-imidazolin-2-yl)-benzo-(6-membered)-heterocycles |
| US5696024A (en) * | 1995-06-06 | 1997-12-09 | American Cyanmid | Herbicidal water soluble granular compositions |
| WO1999013723A1 (en) * | 1997-09-17 | 1999-03-25 | American Cyanamid Company | Synergistic herbicidal methods and compositions |
| US6060430A (en) * | 1997-10-31 | 2000-05-09 | American Cyanamid Company | Methods and compositions for enhancing herbicidal activity |
| US6127317A (en) * | 1997-09-17 | 2000-10-03 | American Cyanamid Company | Concentrated, aqueous herbicidal compositions containing an imidazolinyl acid salt and a glyphosate salt |
| US6214768B1 (en) | 1998-09-14 | 2001-04-10 | American Cyanamid Co. | Synergistic herbicidal methods and compositions |
| US6277787B1 (en) | 1998-09-14 | 2001-08-21 | American Cyanamid Co. | Synergistic herbicidal methods and compositions |
| AU744571B2 (en) * | 1997-10-31 | 2002-02-28 | American Cyanamid Company | Methods and compositions for enhancing herbicidal activity |
| US20020107149A1 (en) * | 2000-12-01 | 2002-08-08 | Greg Volgas | Manufacture and use of a herbicide formulation |
| US6703346B2 (en) * | 2001-09-26 | 2004-03-09 | Platte Chemical Co. | Herbicide compositions comprising imidazolinone acid, methods of preparation, and methods of use |
| US20050288188A1 (en) * | 2004-06-28 | 2005-12-29 | Helena Holding Company | Manufacture and use of a plant growth regulating compound |
| US20060270557A1 (en) * | 2005-05-27 | 2006-11-30 | Helena Holding Company | Herbicide formulation |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5250502A (en) * | 1990-04-30 | 1993-10-05 | American Cyanamid Company | Method for enhancing the herbicidal activity of formulations containing solid imidazolinyl benzoic acid esters with bisulfate |
| EP0454968A1 (en) * | 1990-04-30 | 1991-11-06 | American Cyanamid Company | Method for enhancing the biological activity of formulations containing solid imidazolinyl benzoic acid esters |
| EP0473890A1 (en) * | 1990-08-28 | 1992-03-11 | American Cyanamid Company | Aqueous herbicidal compositions of 2-(2-imidazolin-2-yl)-pyridines and quinolines |
| DK0554015T3 (da) * | 1992-01-28 | 1995-06-06 | Ishihara Sangyo Kaisha | Kemisk stabiliseret herbicidisk olie-baseret suspension |
| AU2003229178A1 (en) * | 2002-05-13 | 2003-11-11 | Ceres Environmental Solution Industry Incorporated | Urea based natural herbicide compositions |
| UA120654C2 (uk) | 2018-01-15 | 2020-01-10 | Олександр Юрійович Микитюк | Спосіб очистки рідких вуглеводневих моторних палив або вуглеводневих паливних фракцій від сірки |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4188487A (en) | 1977-08-08 | 1980-02-12 | American Cyanamid Company | Imidazolinyl benzoic acids, esters and salts and their use as herbicidal agents |
| US4297128A (en) * | 1978-06-09 | 1981-10-27 | American Cyanamid Co. | Use of imidazolinyl benzoates as herbicidal agents |
| US4488896A (en) * | 1980-03-13 | 1984-12-18 | American Cyanamid Company | Methods and compositions for the selective control of undesirable weed species in the presence of wet-land crops |
| DE3162095D1 (en) * | 1980-06-02 | 1984-03-08 | American Cyanamid Co | Method to beneficially influence & alter the development & life cycle of agronomic and horticultural crops with certain imidazolinyl nicotinic acids and derivatives thereof |
| FI860449A (fi) * | 1985-02-04 | 1986-08-05 | American Cyanamid Co | Komposition foer behandling av graesmatta. |
| ATE84533T1 (de) * | 1985-12-13 | 1993-01-15 | American Cyanamid Co | Neue kondensierte pyridinverbindungen, zwischenverbindungen fuer die herstellung und ihre verwendung als herbizide wirkstoffe. |
-
1986
- 1986-08-15 US US06/896,775 patent/US4816060A/en not_active Expired - Lifetime
-
1987
- 1987-08-04 ES ES198787111215T patent/ES2037686T3/es not_active Expired - Lifetime
- 1987-08-04 DE DE8787111215T patent/DE3776833D1/de not_active Expired - Lifetime
- 1987-08-04 EP EP87111215A patent/EP0256414B1/en not_active Expired - Lifetime
- 1987-08-04 AT AT87111215T patent/ATE72727T1/de not_active IP Right Cessation
- 1987-08-06 IL IL83461A patent/IL83461A/xx not_active IP Right Cessation
- 1987-08-11 IN IN624/CAL/87A patent/IN166550B/en unknown
- 1987-08-12 TR TR87/0569A patent/TR24598A/xx unknown
- 1987-08-13 CS CS875979A patent/CS271478B2/cs not_active IP Right Cessation
- 1987-08-13 CA CA000544404A patent/CA1297695C/en not_active Expired - Lifetime
- 1987-08-13 EG EG469/87A patent/EG18433A/xx active
- 1987-08-13 YU YU151187A patent/YU46560B/sh unknown
- 1987-08-14 BR BR8704215A patent/BR8704215A/pt not_active IP Right Cessation
- 1987-08-14 JP JP62201952A patent/JP2512759B2/ja not_active Expired - Lifetime
- 1987-08-14 DD DD87306062A patent/DD261518A5/de unknown
- 1987-08-14 IE IE217687A patent/IE61158B1/en not_active IP Right Cessation
- 1987-08-14 AU AU76892/87A patent/AU597407B2/en not_active Expired
- 1987-08-14 HU HU873684A patent/HU200888B/hu unknown
- 1987-08-14 KR KR1019870008947A patent/KR950006916B1/ko not_active IP Right Cessation
- 1987-08-14 DK DK198704257A patent/DK174864B1/da not_active IP Right Cessation
- 1987-08-14 BG BG080934A patent/BG48203A3/xx unknown
- 1987-08-14 ZA ZA876050A patent/ZA876050B/xx unknown
- 1987-08-14 UA UA4203183A patent/UA6153A1/ru unknown
- 1987-08-14 SU SU874203183A patent/SU1723994A3/ru active
-
1992
- 1992-02-27 GR GR910401738T patent/GR3003891T3/el unknown
-
1994
- 1994-01-20 GE GEAP19941747A patent/GEP19970806B/en unknown
Non-Patent Citations (1)
| Title |
|---|
| Adalla et al. Chem. Abst. vol. 93 (1980), 90069b. * |
Cited By (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4936902A (en) * | 1989-04-25 | 1990-06-26 | American Cyanamid Company | Selective control of sicklepod in the presence of leguminous crops |
| US5268352A (en) * | 1989-11-22 | 1993-12-07 | American Cyanamid Company | Herbicidal emulsifiable suspension concentrate compositions |
| US5397766A (en) * | 1989-11-22 | 1995-03-14 | American Cyanamid Company | Herbicidal emulsifiable suspension concentrate compositions |
| US5283335A (en) * | 1990-08-31 | 1994-02-01 | American Cyanamid Company | Herbicidal 2-(2-imidazolin-2-yl)-benzo-(6-membered)-heterocycles |
| US5696024A (en) * | 1995-06-06 | 1997-12-09 | American Cyanmid | Herbicidal water soluble granular compositions |
| US6127317A (en) * | 1997-09-17 | 2000-10-03 | American Cyanamid Company | Concentrated, aqueous herbicidal compositions containing an imidazolinyl acid salt and a glyphosate salt |
| WO1999013723A1 (en) * | 1997-09-17 | 1999-03-25 | American Cyanamid Company | Synergistic herbicidal methods and compositions |
| US6060430A (en) * | 1997-10-31 | 2000-05-09 | American Cyanamid Company | Methods and compositions for enhancing herbicidal activity |
| AU744571B2 (en) * | 1997-10-31 | 2002-02-28 | American Cyanamid Company | Methods and compositions for enhancing herbicidal activity |
| US6214768B1 (en) | 1998-09-14 | 2001-04-10 | American Cyanamid Co. | Synergistic herbicidal methods and compositions |
| US6277787B1 (en) | 1998-09-14 | 2001-08-21 | American Cyanamid Co. | Synergistic herbicidal methods and compositions |
| US20020107149A1 (en) * | 2000-12-01 | 2002-08-08 | Greg Volgas | Manufacture and use of a herbicide formulation |
| US20040167032A1 (en) * | 2000-12-01 | 2004-08-26 | Greg Volgas | Manufacture and use of a herbicide formulation |
| US8232230B2 (en) | 2000-12-01 | 2012-07-31 | Helena Holding Company | Manufacture and use of a herbicide formulation |
| US6703346B2 (en) * | 2001-09-26 | 2004-03-09 | Platte Chemical Co. | Herbicide compositions comprising imidazolinone acid, methods of preparation, and methods of use |
| US6803345B2 (en) * | 2001-09-26 | 2004-10-12 | Platte Chemical Co. | Herbicide microemulsion-forming-concentrates, microemulsions, and methods |
| US6906004B2 (en) * | 2001-09-26 | 2005-06-14 | Platte Chemical Co. | Herbicide composition comprising herbicide compound in acid form and acidifying agent |
| US20050170967A1 (en) * | 2001-09-26 | 2005-08-04 | Parrish Scott K. | Herbicide composition comprising herbicide compound in acid form and acidifying agent |
| US7094735B2 (en) | 2001-09-26 | 2006-08-22 | Platte Chemical Co. | Herbicide microemulsion-forming-concentrates, microemulsions, and methods |
| US20060205601A1 (en) * | 2001-09-26 | 2006-09-14 | Herold Anthony E | Herbicide microemulsion-forming-concentrates, microemulsions, and methods |
| US20100184599A1 (en) * | 2001-09-26 | 2010-07-22 | Platte Chemical Company | Herbicide composition comprising herbicide compound in acid form and acidifying agent |
| US20040127364A1 (en) * | 2001-09-26 | 2004-07-01 | Herold Anthony E. | Herbicide compositions comprising imidazolinone acid, methods of preparation, and methods of use |
| US8759256B2 (en) | 2001-09-26 | 2014-06-24 | Platte Chemical Company | Herbicide composition comprising herbicide compound in acid form and acidifying agent |
| US9237746B2 (en) | 2001-09-26 | 2016-01-19 | Platte Chemical Co. | Herbicide composition comprising herbicide compound in acid form |
| US20050288188A1 (en) * | 2004-06-28 | 2005-12-29 | Helena Holding Company | Manufacture and use of a plant growth regulating compound |
| US20060270557A1 (en) * | 2005-05-27 | 2006-11-30 | Helena Holding Company | Herbicide formulation |
| US8426341B2 (en) | 2005-05-27 | 2013-04-23 | Helena Holding Company | Herbicide formulation |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4816060A (en) | Herbicidal aqueous compositions of imidazolinone herbicides | |
| EP1884511B1 (en) | Aromatic ether compounds,preparation and usage thereof | |
| KR100255682B1 (ko) | 신규 페닐피라졸 살진균제 | |
| AU2009329825B2 (en) | Auxin herbicide composition | |
| CA1287570C (en) | Aqueous suspension concentrate compositions of pendimethalin | |
| EP0760208B1 (en) | Compositions having synergistic fungitoxic effects | |
| JPH08501320A (ja) | 農業用調製物 | |
| JPS60181053A (ja) | ２‐シアノベンゾイミダゾールの新規誘導体、その製法及び殺菌剤としての使用 | |
| HU191626B (en) | Process for preparing 2-/5,5-disubstituted-4-oxo-2-imidazolin-2-il/-benzoic acid, -nicotinic acid and -quinoline-3-carboxylic acid derivatives | |
| US6127317A (en) | Concentrated, aqueous herbicidal compositions containing an imidazolinyl acid salt and a glyphosate salt | |
| EP0191514B1 (en) | Imidazole derivatives, their preparation and their use as fungicides | |
| JPS61103873A (ja) | 新規な２‐シアノベンズイミダゾール誘導体 | |
| CA1272612A (en) | Turfgrass management compositions | |
| US4871388A (en) | Herbicidal liquid concentrate compositions | |
| JPH0479337B2 (ru) | ||
| CA2468325A1 (en) | Herbicide composition | |
| US5104873A (en) | Pesticide composition | |
| AU2019345216B2 (en) | Dicyclanil salt with dodecylbenzenesulfonate and use of such a salt in combating and controlling of parasites | |
| US4936902A (en) | Selective control of sicklepod in the presence of leguminous crops | |
| AU631029B2 (en) | Pesticide composition | |
| EP0473890A1 (en) | Aqueous herbicidal compositions of 2-(2-imidazolin-2-yl)-pyridines and quinolines | |
| SI8711511A8 (sl) | Postopek za povečanje stabilnosti vodnih raztopin soli imidazolinonskih kislin | |
| SK281366B6 (sk) | Vodná suspenzná koncentrovaná pesticídna kompozícia a spôsob jej výroby | |
| JPH0586363B2 (ru) | ||
| KR930010032A (ko) | 제초제용 술포닐우레아 유도체와 그의 제조방법 및 이를 포함하는 제초제 조성물과 이를 사용한 제초방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: AMERICAN CYANAMID COMPANY, 1937 WEST MAIN STREET, Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:STELLER, WILLIAM S.;KEINTZ, ROGER C.;REEL/FRAME:004593/0141 Effective date: 19860808 Owner name: AMERICAN CYANAMID COMPANY, A CORP. OF MAINE,CONNEC Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:STELLER, WILLIAM S.;KEINTZ, ROGER C.;REEL/FRAME:004593/0141 Effective date: 19860808 |
|
| FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
| FPAY | Fee payment |
Year of fee payment: 4 |
|
| FPAY | Fee payment |
Year of fee payment: 8 |
|
| FPAY | Fee payment |
Year of fee payment: 12 |
|
| AS | Assignment |
Owner name: BASF AKTIENGESELLSCHAFT, NORTH CAROLINA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:AMERICAN CYANAMID COMPANY;REEL/FRAME:012276/0001 Effective date: 20011017 |
|
| AS | Assignment |
Owner name: BASF AGROCHEMICAL PRODUCTS B.V., NETHERLANDS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BASF AKTIENGESELLSCHAFT;REEL/FRAME:018911/0588 Effective date: 20060815 |